A vehicle transportation system may include multiple vehicles that travel on the same routes. The vehicles may have different characteristics, such as power outputs and weights, that affect how quickly the vehicles can navigate through the routes. A trailing vehicle traveling along a given route may reduce the distance between the trailing vehicle and a slower-moving vehicle ahead of the trailing vehicle along the same route. The trailing vehicle has an incentive to reduce the total trip time in order to meet a designated arrival time at a destination, improve fuel economy, reduce emissions, and the like. Therefore, the trailing vehicle may move according to a trip plan that factors various objectives, such as reducing travel time, reducing fuel consumption, reducing emissions, and the like, while satisfying designated hard constraints, such as upper speed limits. The trailing vehicle traveling according to a trip plan may cause the trailing vehicle to creep up on the vehicle ahead. If the trailing vehicle gets too close to the vehicle ahead, the trailing vehicle may be required to slow to a stop for a designated period of time in order to avoid the risk of an accident between the two vehicles by increasing the distance therebetween. For example, if the vehicles are trains traveling in the same direction on a single track, they are required to avoid occupying the same section of track, called a block. If the trailing vehicle approaches a block that is occupied by the vehicle ahead, the trailing vehicle may be forced to stop before entering the occupied block. The stop is undesirable because such a stop may result in a significant delay that frustrates the ability of the trailing vehicle to satisfy the various objectives, such as reducing travel time, reducing fuel economy, arriving at a destination at or before a prescribed arrival time, and/or the like. Furthermore, having to stop indicates that the trailing vehicle could have reduced speed during an earlier segment of the trip, which could have resulted in considerable fuel savings while arriving at a destination at a similar time as the trailing vehicle traveling faster but having to stop. Due to required slow orders or stops every time the trailing vehicle approaches the vehicle ahead, the trailing vehicle may move along the route in an undesirable “hurry up and wait” manner.